Photos: A Visit to San Juan, Puerto Rico

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THE CONVERGENCE OF old and new is a hallmark of nearly all cities, but nowhere in the U.S. is this coupling as dramatic as in San Juan. Founded in 1521, Puerto Rico's capital is the oldest metropolis in the country's jurisdiction (Puerto Rico maintains a commonwealth status)—and it has the 16th-century sandstone walls and fortifications to prove it. Yet San Juan vibrates with a life force that keeps it from being mistaken for a sleepy monument town. Stroll from Old San Juan to the sandy stretches of Ocean Park and listen to the hip hop-Latin-reggae rhythms of Reggaeton intermingled with a distinct Spanglish lexicon (people "jangear," meaning "to hang out," and act "gufeao," or goofy).

Festivals are on a near-constant rotation. This weekend kicks off the 57th annual Casals Festival, a celebration of classical music, and the Heineken Jazz Festival follows on its heels. Those with a hunger for local cuisine like tostones (fried green plantains) and asopao (rice stew), should check out the Saborea food festival, an annual celebration of chefs and local cuisine taking place in early April. Jose Enrique, a humble restaurant located in an old home and known for crab cakes that can inspire three-hour lines, has even made it onto the list of semifinalists for the 2013 James Beard Foundation Awards, the first year Puerto Rico has been eligible.

Make sure to visit Santurce, a once-gritty district that draws a fashionable, arty crowd. Start the night with a plate of fish tacos at Tresbe, a joint housed in a shipping container; sip a café con leche at Kamoli Café, a coffee spot that doubles as a bohemian boutique and gallery; then end the night at La Respuesta performance space. Keep your eyes open: The island has seen a rise in drug-related crime in recent years. And don't forget to go to the beach.

—Kathleen Squires

The Experts

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The Actor: Benicio Del Toro

Oscar-winning actor for "Traffic," co-star of the 2012 film "Savages"; San Juan native

Salsa Sanctuary // Viera Discos. Salsa musicians love to hang out at this great record and CD store. Sometimes they'll give live performances right in the shop. The store is known as the "cathedral of Latin music" because it's in an old church. 909 Avenida Manuel Fernández Juncos, Miramar, 787-725-1105

Literary Lion // Libreria La Tertulia. There aren't many bookstores in San Juan anymore. This one has lasted over 40 years. They have a great selection of Spanish-language books focused on the humanities, literature and social sciences. 1002 Avenida Ponce de León, Río Piedras, tertulia.com

Art and Eats // Museo de Arte de Puerto Rico. I love spending the day looking at the collection of Puerto Rican and Latin American artists. And there's a great restaurant, Laurel Kitchen: Art Bar, run by Mario Pagán—one of Puerto Rico's leading chefs. 299 Avenida De Diego, Santurce, mapr.org

Surf Style // Tres Palmas. Conveniently located one block from the beach, this is the place to pick up swim trunks, bikinis, sunglasses, surfboards and any other kind of watersports equipment. 1911 Avenida McLeary, Ocean Park, trespalmaspr.com

Juke Joint // El Batey. For drinks, I like places that come with music. This dive is full of character and has a classic rock 'n' roll jukebox. The walls are covered in graffiti, there is a pool table and it's right in the middle of the Old City. 101 Calle del Cristo, Old San Juan 787-723-7657

The Cook: Carmen González

Chef and owner of Carmen at the Danforth in Portland, Maine; grew up in San Juan and Aguadilla

Room with View // Hotel El Convento. Once a 17th-century convent, this is now the most atmospheric hotel in the city. Get a room facing the cathedral or overlooking the Plazuela de Las Monjas. 100 Calle del Cristo, Old San Juan, elconvento.com

Earlier

Puerto Rico is seeing a new wave of luxury development as the government implements tax incentives. WSJ's Alyssa Abkowitz takes a look. Photo: St Regis Bahia Beach Resort. (10/4/2012)

Pirate Portal // La Puerta de San Juan. I get the chills when I think of all the people who entered the walled city through this door—pirates, slaves and explorers. The only remaining city gate, it's huge and towering with thick walls. Paseo de la Princesa and Calle San Juan, Old San Juan

Fruit Loop // La Plaza del Mercado, Santurce. The best way to get to know all of our fruits and vegetables is to walk through the market we call "La Placita." Ask the vendors to tell you the names of the different varieties of tropical produce—they might not be bilingual but they know the English words for what they are selling. 78 Dos Hermanos and Calle Capitol, Santurce, placitasanturce.com

Coffee Stop // Kasalta. When I was growing up, a weekend tradition was to stop here for a little coffee, go to the beach, then come here to lunch on a monster sandwich. 1966 Avenida McLeary, Ocean Park, kasalta.com

Last Chance Snack // Panaderia España. Whenever I'm on the way to the airport, I have to stop here for a medianoche, which is a ham, pork, cheese, mustard and pickle sandwich. It's like a Cuban sandwich but with a sweeter, softer bread. 1105 Marginal Villamar, Isla Verde, panaderiaespanapr.com

The Athlete: Javier Culson

Ponce-born Bronze medalist in hurdling, 2012 Olympic Games

Mashup Meal // Restaurante Raíces. This is a great spot to try mofongo, which is mashed green plantains stuffed with fish or meat and served in a traditional wooden mortar and pestle. 315 Calle Recinto Sur, Old San Juan, restauranteraices.com

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Restaurante Raíces
Angel Valentin for The Wall Street Journal

Precious Panoramas // Paseo de la Princesa. Walk along this promenade and get a sense of the city's history through vistas of the forts and old city walls. There are also gorgeous views of the bay. Stretches from Calle La Puntilla and Calle Tizol to La Puerta de San Juan, Old San Juan

Best Beach // El Escambrón. This beach is popular with kite surfers. The water is so blue and clear, which means it's ideal for snorkeling, too. Alongside Avenida Muñoz Rivera, Puerta de Tierra

Jet Eyes // Aquatica. Jet skiing in the bay of San Juan with the old city in front of you is a rush. The guides at this tour company will point out the city's historic attractions. Avenida Fernandez Juncos 8 at Puente Dos Hermanos, 787-531-3593

Family Fun // Museo del Niño. The children's museum is fun no matter how old you are. Interactive exhibits explore space travel and how the human body works. 150 Calle Cristo, Old San Juan, museodelninopr.org

Living Landmark // La Fortaleza. Originally built as a fort to protect the city in the 1500s, La Fortaleza is now where the island's governor lives. It's a Unesco World Heritage site and visitors can tour the grounds. Calle Fortaleza, Old San Juan, nps.gov

The Musician: Olga Tañón

Must-do Monument // Castillo San Felipe del Morro. We have a saying: "If you haven't visited El Morro, you haven't been to Puerto Rico." Dating back to the 16th century, this fort is magnificent and historically significant. Calle Norzagaray, Old San Juan, nps.gov

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Barrachina
Angel Valentin for The Wall Street Journal

Performance Palace // Teatro Tapia. The Festival of Puerto Rican Theater takes place here, as do many operas, ballets and plays. The interior is very grand, like a classic old opera house. Calle Fortaleza and Plaza de Colón, Old San Juan, teatropr.com

Tropical Happy Hour // Barrachina. It's said that the piña colada was invented at this bar and restaurant. The drink is emblematic of Puerto Rico—pineapple, coconut and rum basically make up our landscape. 104 Calle Fortaleza, Old San Juan, barrachina.com

House of the Holy // Catedral San Juan Bautista. This 500-year-old cathedral is featured in one of my music videos, "Hoy Quiero Confesarme." The tomb of Juan Ponce de León is inside, and the holiday services here are magnificent. 151 Calle Cristo, Old San Juan, catedralsanjuan.com

Organic Artifacts // Museo Arte e Historia de San Juan. This museum boasts a lovely collection of Puerto Rican art. Its permanent exhibit offers an audiovisual lesson on the city's history. The city's only organic farmers' market is held within its courtyard on Saturday mornings. 150 Calle Norzagaray, Old San Juan, mercadoagricolanatural.com

Plus Don't Miss...

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Stella Nolasco The new shop by the island's premier women's clothing designer carries edgy couture. stellanolasco.com // Condado Vanderbilt Hotel Once the property of Frederick William Vanderbilt, this freshly restored hotel recently opened its restaurant, 1919, and cigar bar, Avo Lounge. condadovanderbilt.com // O: live Boutique Hotel The Mediterranean meets the Caribbean at this 15-room hotel. Its rooftop features two Jacuzzis, a lap pool and a grill—along with stunning views of the Condado Lagoon. oliveboutiquehotel.com // Antique Chocolates This shop features locally made treats with tropical fillings, such as guava and "coquito" (Puerto Rican eggnog). antiquechocolates.com

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